Considering that Webster published his first dictionary in 1806, is there a recognised tipping point (year, decade, etc.) that marked the move from traditional British spelling to Webster's American? Was this shift a gradual but chaotic process or was it a deliberate and possibly collective decision taken by the educational institutions, the media, or the government of the time? In other words, how did the shift come about?

2 Answers
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No, there was not a a deliberate and possibly collective decision taken by the educational institutions, the media, or the government of the time.

Yes, there were a few changes that Webster tried, but the history of English spelling is much, much, much more complicated than that. English has never had a single agreed-upon spelling, even within any one country. There is no such thing as the American spelling, nor for that matter is there the British spelling, when discussing the English language. At most, there are individual words that may show a general predilection, but that shifts over time and within writers and publishers. It isn’t a simple us-vs-them situation almost in any pairing. There is too much historical variation.

There is a lot more variation than even that summary shows; please see the more detailed charts below, including some that go the other way by showing British usage. Each of these really is a separate case, and must be considered individually. There is no single, solitary, discrete, and agreed-upon thing called American spelling versus British spelling. There is a vast continuum of conflicting tendencies, some weaving back and forth time across the Atlantic, and across time. Even when one spelling “supersedes” another, it merely comes out ahead in the popularity contest. It usually does not wholly supplant the former spelling.

For the Ngramaniacs

In all cases, the putative “American” spelling is in blue, and the putative “British” spelling is in red. Notice how the answers are all over the board, and some rather surprising, too.

center vs centre

When did center supersede centre in American English? Answer: Around 1910. Ngram

theater vs theatre

When did theater supersede theatre in American English. Answer: During the late 1970s. Ngram

armor vs armour

When did armor supersede armour in American English? Answer: Around 1850. Ngram

glamor vs glamour

When did glamor supersede glamour in American English? Answer: Never, because it has always been a minority usage. Ngram

woolen vs woollen

When did woolen supersede woollen in American English? Answer: around 1905. Ngram

tire vs tyre

When did tire supersede tyre in American English? Answer: Never, because it was always dominant. Ngram

Well, and when did tyre supersede tire in British English? Answer: in the early 1940s. But it only lasted a couple of decades before falling back into minority usage again. Ngram

miter vs mitre

When did miter supersede mitre in American English? Answer: Around 1920. Then again around 1940. Then again around 1970. Ngram

acknowledgment vs acknowledgement

When did acknowledgment supersede acknowledgement in American English? Never. It has always been that way. Ngram

What about the other way around? When did acknowledgement supersede acknowledgment in British English? Answer: Around 1970. Ngram

scepter vs sceptre

When did scepter supersede sceptre in American English? Answer: Around 1980. Ngram

savior vs saviour

When did savior supersede savior in American English? Answer: Around 1930. Ngram

deputize vs deputise

When did deputize supersede deputise in American English? Answer: Around 1810. Ngram

But what about the other way around? When did deputise supersede deputize in British English? It’s arguable, but the general answer is that it never did. Ngram

ameba vs amoeba

When did ameba supersede amoeba in American English? Answer: Never. Ngram

jewelry vs jewellery

When did jewelry supersede jewellery in American English? Answer: Around 1810. Ngram

connection vs connexion

When did connection supersede connexion in American English? Answer: Around 1845. Ngram

But what about the other way around? When did connexion supersede connection in British English? Answer: Around 1820. But it only did so for around 30 years, up through around 1850. Ngram

colored vs coloured

Since this one seems to be everybody’s favorite peeve, when did colored supersede coloured in American English? Answer: Around 1840. Ngram

leveled vs levelled

When did leveled supersede levelled in American English? Answer: Around 1915. Ngram

fetus vs foetus

When did fetus supersede foetus in American English? Answer: around 1910. Ngram

Hm, but what about the other way around? When did foetus supersede fetus in British English? It didn’t: it gave up the lead around 1970. Ngram

paralyzed vs paralysed

When did paralyzed supersede paralysed in American English? Answer: Always. ngram

And the other way around: when did paralysed supersede paralyzed in British English? Answer, around 1830, but it has been losing a lot of ground recently. Ngram

specter vs spectre

When did specter supersede spectre in American English? Answer: around 1940. Ngram

esophagus vs oesophagus

When did esophagus replace oesophagus in American English? Answer: Around 1910. Ngram

But what about British usage? The answer is that oesophagus seems to have lost to esophagus around 1980, but then may have returned. It’s hard to tell. Ngram

aluminum vs aluminium

When did aluminum supersede aluminium in American English? Answer: around 1900. Ngram

And what about the other way around? When did aluminium supersede aluminum in British English? Answer: around 1850, but it has lost a great deal of ground of late. Ngram

surprize vs surprise

It turns out that surprize was once the dominant form, not surprise, but this didn’t last even a hundred years. Ngram

Then again, here is the British Ngram for the same pair. Notice that even the Brits used the z for a good while, possibly even for longer than in North America:

Summary

I hope you can now see why I said what I said: that there can be no clear answer here. Everything is different. You have to look at each word-pair separately, and you should make sure you aren’t wrong about Britain, either.

Yet there are characteristics of American spelling vs. English spelling; for example, color vs. colour. How did that difference come about?
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MarthaªOct 24 '12 at 16:57

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@tchrist I think many of the trends you mention are examples of words being taken over from other cultures, loanwords. And maybe the differences will be getting smaller and smaller in the future. But that doesn't explain where the differences came from in the first place.
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Mr ListerOct 24 '12 at 18:27

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@tchrist: on the contrary, I think that is exactly the question being asked. The details might be wrong — that's why he's asking, after all — but there seems to have been a process by which American spelling diverged from British spelling. The presence of outliers, iconoclasts, and immigrants doesn't change this fact.
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MarthaªOct 24 '12 at 19:39

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The OP is certainly not the first to suggest that there are many words that Americans spell differently than Britons: this is generally taken as common knowledge and not some radical new theory. Are you seriously saying that this is not true? Yes, yes, you can find cases where an American used the British spelling and vice versa, but that hardly refutes the theory. (Just as it is true that men are generally taller than women, even though there are cases of women who are taller than the average man.) Indeed, the very fact that when I say, "An American used the British spelling of 'colour'" ...
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JayOct 24 '12 at 20:54

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Tire in Britain is almost always related to weariness: cars have tyres. I don't think that weakens your answer (with which I largely agree), but it does weaken the belief that Ngrams are helpful in such cases.
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TimLymingtonDec 25 '12 at 17:03

While the progress of English spelling reform (which is apparently the term of choice) in the United States generally appears to have been gradual and chaotic, three major periods of change through deliberate process seem to be its primary drivers.

Webster's first dictionary, A Compendious Dictionary of the English Language, was published in 1806. He then spent twenty years revising it to produce the first American Dictionary of the English Language (ADEL) which was published in 1828. An expanded and revised second edition appeared in 1841. Although it drew some protest, the reformed spellings were gradually adopted throughout the United States.

"But some remained, and since the book was successful in establishing its authority throughout the States, they have become generally recognized as American forms. In that sense Webster was the first to differentiate between British and American usage, and in that it was frequently he who chose the variant of two spellings in early nineteenth-century use which have subsequently been preferred in the United States, he can be said to have influenced the development of spelling. He is in a way 'responsible' for such forms as center, color and defense."

While Webster championed a number of spelling reforms, only a few were widely adopted.

The release and adoption of the ADEL editions certainly corroborates with a number of ngrams which show the new American spelling steadily becoming popular after the 1820s and eventually becoming more dominant on or after 1845. For example,

There are a number of other similar instances. There are also examples such as fraternize vs. fraternise where the former, while already (in terms of the ngram) maintaining a small lead in preference, takes a sudden leap after ~1835.

As mentioned earlier, only a few of Webster's reforms, of which many were contentious, were adopted. After his death, the more egregious of his changes were gradually dropped by subsequent editors. In the 1870s, the American Spelling Reform Association was formed. They, along with the American Philological Society and the American Philological Association worked further on simplifying (American) English spelling.

That year, the American Philological Society adopted a list of eleven reformed spellings for immediate use. These were: are→ar, give→giv, have→hav, live→liv, though→tho, through→thru, guard→gard, catalogue→catalog, (in)definite→(in)definit, wished→wisht. One major American newspaper that begun using reformed spellings was the Chicago Tribune, whose editor and owner, Joseph Medill, sat on the Council of the Spelling Reform Association. In 1883, the American Philological Society and American Philological Association worked together to produce 24 spelling reform rules, which were published that year. In 1898, the American National Education Association adopted its own list of 12 words to be used in all writings. These were: tho, altho, thoro, thorofare, thru, thruout, catalog, decalog, demagog, pedagog, prolog, program.

1906 saw the formation of the American Spelling Board which was funded by Andrew Carnegie. They published a list of 300 words which were adopted by President Roosevelt for government use.

Roosevelt tried to force the federal government to adopt the system, sending an order to the Public Printer to use the system in all public federal documents. The order was obeyed; among the many documents printed using the system was the President's special message regarding the Panama Canal.

However, in December 1906 the U.S. Congress passed a resolution and the old spellings were reintroduced. Nevertheless, some of the spellings survived and are commonly used in American English today, such as anaemia/anæmia→anemia and mould→mold. Others such as mixed→mixt and scythe→sithe did not survive.

To summarise, the divergence of American spelling is the result of spelling reforms initiated by Webster, taken further by interested parties including at least one media house, and eventually, the (temporary) backing of the US government. However, only a small percentage of each set of proposed reforms were adopted at any one time. The more drastic of reforms met with stiff resistance:

Roosevelt ultimately decided to rescind the order. Brander Matthews, a friend of Roosevelt and one of the chief advocates of the reform as chairman of the Simplified Spelling Board, remonstrated with him for abandoning the effort. Roosevelt replied on December 16, 1906: "I could not by fighting have kept the new spelling in, and it was evidently worse than useless to go into an undignified contest when I was beaten. Do you know that the one word as to which I thought the new spelling was wrong — thru — was more responsible than anything else for our discomfiture?" Next summer Roosevelt was watching a naval review when a press boat marked "Pres Bot" chugged ostentatiously by. The President waved and laughed with delight.